Ethyl Acrylate → Ethyl (2E)-3-(3,4-difluoro-5-hydroxyphenyl)-2-propenoate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.[C:33]([O:37][CH2:38][CH3:39])(=[O:36])[CH:34]=[CH2:35].C(N(C(C)C)CC)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2].C(#N)CC>[F:10][C:4]1[CH:3]=[C:2](/[CH:35]=[CH:34]/[C:33]([O:37][CH2:38][CH3:39])=[O:36])[CH:7]=[C:6]([OH:8])[C:5]=1[F:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A second 1 L round-bottomed flask was charged with a stir bar, 5-bromo-2,3-difluorophenol (50.2 g, 240 mmol) and propionitrile (460 mL). The solution was deoxygenated by bubbling nitrogen for 15 minutes. To this solution was added Pd(OAc)2 (5.42 g, 24.1 mmol), P(O-tol)3 (29.3 g, 96.1 mmol), ethyl acrylate (52 mL, 480 mmol) and diisopropylethylamine (167 mL, 959 mmol) sequentially. The flask was immersed into a preheated (120° C.) oil bath. The reaction was heated at this temperature for 22 h. Upon cooling to room temperature, the reaction mixture was filtered through a Celite-plugged filter frit, washed with CH2Cl2, and concentrated.
Workup
- additionA second 1 L round-bottomed flask was charged with a stir bar
- customThe solution was deoxygenated
- customby bubbling nitrogen for 15 minutes
- customwas immersed into a preheated (120° C.) oil bath
- temperatureThe reaction was heated at this temperature for 22 h
- filtrationthe reaction mixture was filtered through a Celite-plugged filter frit
- washwashed with CH2Cl2
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c0e8ab50027b4c5bb2e0521531b03645
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902394B2
Reaction notes
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